Malic acid

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O5
Molecular Weight	134.0874
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H6O5
Molecular Weight	134.0874
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://gov.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/FR330.pdf | https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdfhttp://www.cosmeticsinfo.org/ingredient/sodium-malate | https://www.food.gov.uk/science/additives/enumberlist#h_7 | https://www.ncbi.nlm.nih.gov/pubmed/11358110 | https://www.ncbi.nlm.nih.gov/pubmed/9477166

Malic acid is a tart-tasting organic dicarboxylic acid that contributes to the taste of many sour or tart foods such as apples. Sodium Malate is the sodium salt of Malic Acid. Malic Acid and Sodium Malate can be found in a wide range of cosmetics and personal care products. Sodium Malate functions as a skin conditioning agent-humectant. As a food additive, Sodium Malate has the E number E350. Sodium Malate has demonstrated protective effect on cisplatin-induced toxicity in mice. Sodium malate could become a useful agent for the reduction of CDDP-induced toxicity, particularly nephrotoxicity and hepatotoxicity.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cisplatin-induced toxicity 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9477166 https://www.ncbi.nlm.nih.gov/pubmed/9514605	Secondary	Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8974556 https://www.ncbi.nlm.nih.gov/pubmed/1458176	Preventing	Preclinical	Unknown Approved Use Unknown
Skin injuries 8 Sources: https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf	Curative	Approved 8429	ACERBINE Approved Use Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.

PubMed

Title	Date	PubMed
Metabolic regulation of pH in plant cells: role of cytoplasmic pH in defense reaction and secondary metabolism.	2001	11407758
Effect of an antidiabetic extract of Catharanthus roseus on enzymic activities in streptozotocin induced diabetic rats.	2001 Aug	11448549
Carbohydrate deprivation reduces NADPH-production in fish liver but not in adipose tissue.	2001 Aug	11404182
Exercise and ovarian steroid hormones: their effects on mitochondrial respiration.	2001 Feb 16	11253167
Poly-beta-hydroxybutyrate metabolism is affected by changes in respiratory enzymatic activities due to cold stress in two psychrotrophic strains of Rhizobium.	2001 Jan	11116398
Cat8 and Sip4 mediate regulated transcriptional activation of the yeast malate dehydrogenase gene MDH2 by three carbon source-responsive promoter elements.	2001 Jan 30	11169757
Malo-ethanolic fermentation in grape must by recombinant strains of Saccharomyces cerevisiae.	2001 Jul	11447602
The first examples of (S)-2-hydroxyacid dehydrogenases catalyzing the transfer of the pro-4S hydrogen of NADH are found in the archaea.	2001 Jul 9	11451450
Inducible and constitutive expression using new plasmid and integrative expression vectors for Thermus sp.	2001 Jun	11412354
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
Energetic determinants of tyrosine phosphorylation of focal adhesion proteins during hypoxia/reoxygenation of kidney proximal tubules.	2001 Jun	11395393
What controls the outer mitochondrial membrane permeability for ADP: facts for and against the role of oncotic pressure.	2001 Jun 1	11334786
Myoadenylate deaminase deficiency does not affect muscle anaplerosis during exhaustive exercise in humans.	2001 Jun 15	11410643
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.	2001 Jun 29	11434921
The homeodomain proteins PBX and MEIS1 are accessory factors that enhance thyroid hormone regulation of the malic enzyme gene in hepatocytes.	2001 Jun 29	11331288
Non-photosynthetic 'malic enzyme' from maize: a constituvely expressed enzyme that responds to plant defence inducers.	2001 Mar	11352460
Supply of O2 regulates demand for O2 and uptake of malate by N2-fixing bacteroids from soybean nodules.	2001 Mar	11238973
Effect of the herbicide glyphosate on enzymatic activity in pregnant rats and their fetuses.	2001 Mar	11237511
Induction of the mitochondrial permeability transition mediates the killing of HeLa cells by staurosporine.	2001 Mar 15	11289115
Identification of the human mitochondrial oxodicarboxylate carrier. Bacterial expression, reconstitution, functional characterization, tissue distribution, and chromosomal location.	2001 Mar 16	11083877
[Properties of gluconeogenesis enzymes from flatworms].	2001 Mar-Apr	11452789
Cloning and functional characterization of the 5' flanking region of the human mitochondrial malic enzyme gene. Regulatory role of Sp1 and AP-2.	2001 May	11358520
Oxyconformity in the intertidal worm Sipunculus nudus: the mitochondrial background and energetic consequences.	2001 May	11337254
High frequency of cytolytic T lymphocytes directed against a tumor-specific mutated antigen detectable with HLA tetramers in the blood of a lung carcinoma patient with long survival.	2001 May 1	11325844
Assimilation of D-malate by Rhodobacter capsulatus E1F1.	2001 Sep	11400062

Patents

Sample Use Guides

In Vivo Use Guide

Apply Acerbine solution (malic acid, salicylic acid, benzoic acid) to the wound or damaged skin two or more times daily or moisten the dressing again. Once scar formation begins, one application a day is generally sufficient.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:34 GMT 2023`
Record UNII	817L1N4CKP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Malic acid

Official Name

English

MALIC ACID [USP IMPURITY]

Common Name

English

MALIC ACID, DL-

Common Name

English

POMALOUS ACID

Common Name

English

INS NO.296

Code

English

MALIC ACID [VANDF]

Common Name

English

MALATE

Common Name

English

MALIC ACID [INCI]

Common Name

English

MALIC ACID [USP-RS]

Common Name

English

DL-MALIC ACID

Common Name

English

HYDROXYBUTANEDIOIC ACID, (±)-

Systematic Name

English

MALIC ACID [FCC]

Common Name

English

E-296

Code

English

NSC-25941

Code

English

INS NO. 296

Code

English

E296

Code

English

(±)-MALIC ACID

Common Name

English

MALIC ACID [II]

Common Name

English

MALIC ACID [EP MONOGRAPH]

Common Name

English

HYDROXYBUTANEDIOIC ACID [HSDB]

Common Name

English

INS-296

Code

English

MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]

Common Name

English

D,L-MALIC ACID

Common Name

English

Malic acid [WHO-DD]

Common Name

English

HYDROXYSUCCINIC ACID

Common Name

English

MALIC ACID [MI]

Common Name

English

2-HYDROXYBUTANEDIOIC ACID

Systematic Name

English

MALIC ACID [NF]

Common Name

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-296